Undecylenic acid

Undecylenic acid
Names
IUPAC name
Undec-10-enoic acid
Other names
10-Undecenoic acid
Identifiers
ATC code D01AE04
112-38-9 Yes
ChEBI CHEBI:35045 Yes
ChemSpider 10771160 Yes
Jmol-3D images Image
MeSH Undecylenic+acid
PubChem 5634
UNII K3D86KJ24Nk 
Properties
Molecular formula
 C11H20O2
Molar mass 184.28 g·mol−1
Density 0.912 g/mL
Melting point 23 °C (73 °F; 296 K)
Boiling point 275 °C (527 °F; 548 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
Infobox references

Undecylenic acid is an organic unsaturated fatty acid pyrolysis product of ricinoleic acid from castor oil. It is the common name of 10-undecenoic acid, (CH2CH(CH2)8COOH). It is used in the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos, antimicrobial powders and as a musk in perfumes and aromas.[1] Undecylenic acid is produced by cracking of castor oil under pressure.[2]

Medicinal uses

In the United States, undecylenic acid is not FDA-approved for over-the-counter use for skin disorders or skin problems.[3]

Undecylenic acid is the active ingredient in medications for skin infections, and relieves itching, burning, and irritation. For example, it is used against fungal skin infections,[3] such as athlete's foot, ringworm, jock itch or Candida albicans. When used for jock itch, it can result in extreme burning, as the skin is rather sensitive. In some case studies of Tinae Versicolor pain and burning upon fungicide application is due to the adaptive reactions typical to many fungi when threatened by a chemical to which it has biochemical phobic repulsion, or similarly to a threat made by the host's effective immune system response, and/or due to the lipoids, toxic to the host, that are naturally released by many fungus at the time death. In these cases burning was simply an indication that the fungicide was effectively treating the infection in the area of skin where it was applied.

At least one of the mechanisms underlying its antifungal effects observed is its inhibition of morphogenesis of Candida albicans. In a study on denture liners, undecylenic acid in the liners was found to inhibit conversion of yeast to the hyphal form. Hyphae were associated with active infection. The mechanisms of action appear to be interference with fatty acid biosynthesis, which can inhibit germ tube (hyphae) formation. Medium-chain fatty acids have also been shown to disrupt the pH of the cell cytoplasm by being proton carriers, which interferes with viral replication mechanisms in infected cells. The mechanism of action and effectiveness in fatty acid based antifungals is dependent on the number of carbon atoms in the chain, being more effective as the number of atoms in the chain increases (undecylenic acid has 11).[4]

Other uses

Undecylenic acid can be used in silicon-based biosensors. Monolayers can be made on bare silicon transducer surfaces with the help of covalent bonds between silicon atom and the double bonds of undecylenic acid. The carboxylic acid groups remain available for the conjugation of biomolecules such as DNA or proteins.[5]

References

  1. ↑ "United States International Trade Commission Memorandum" (PDF). USITC. Archived from the original (PDF) on 2006-09-24. Retrieved 2007-01-02. - see page 2 of link
  2. ↑ Lemuel P. Ereaux and Gibson E. Craig (1949). "Undecylenic Acid in Psoriasis". Can Med Assoc J. 61 (4): 361–364. PMC 1591667. PMID 18140580.
  3. ↑ 3.0 3.1 "Ingredient List P-Z" (PDF). FDA (see page 65 of this link). Archived from the original (PDF) on 2006-10-16. Retrieved 2006-12-28.
  4. ↑ "Undecyclic Acid". Retrieved 2008-07-09.
  5. ↑ A. Moraillon, A. C. Gouget-Laemmel, F. Ozanam, and J.-N. Chazalviel (2008). "Amidation of Monolayers on Silicon in Physiological Buffers: A Quantitative IR Study". J. Phys. Chem. C 112 (18): 7158–7167. doi:10.1021/jp7119922.